Deals on vacations and trips to Winchester

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Price found within the past 48 hours. Click for updated prices.
Comfort Suites Southport

Comfort Suites Southport

2.5 out of 5
Price was $227, price is now $178 per person
$178
per person
Feb 20 - Feb 22
found 5 hours ago
Roundtrip flight included
Denver (DEN) to Indianapolis (IND)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like self-serve breakfast and free self parking.
Graduate by Hilton Bloomington

Graduate by Hilton Bloomington

4 out of 5
Price was $775, price is now $581 per person
$581
per person
Feb 6 - Feb 9
found 11 hours ago
Roundtrip flight included
Denver (DEN) to Indianapolis (IND)
A 24-hour gym is featured at this hotel, along with valet parking. WiFi in public areas is free. A coffee shop, dry cleaning, and luggage storage are also on offer.
Grant Street Inn

Grant Street Inn

3.5 out of 5
Old Northeast Downtown
Price was $615, price is now $470 per person
$470
per person
Feb 6 - Feb 9
found 11 hours ago
Roundtrip flight included
Denver (DEN) to Indianapolis (IND)
A 24-hour gym, free self parking, and free newspapers are featured at this bed & breakfast. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A library and luggage storage are also provided.
Landing Apartments - Lebanon, IN

Landing Apartments - Lebanon, IN

3 out of 5
Price was $679, price is now $528 per person
$528
per person
Feb 13 - Feb 16
found 10 hours ago
Roundtrip flight included
Denver (DEN) to Indianapolis (IND)
This apartment features a gym and a seasonal outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A lobby fireplace, a library, and barbecue grills are also on offer.
Hotel Nashville

Hotel Nashville

2.5 out of 5
Price was $420, price is now $343 per person
$343
per person
Feb 6 - Feb 9
found 11 hours ago
Roundtrip flight included
Denver (DEN) to Indianapolis (IND)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.

Top Winchester hotels deals

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA

Winchester IN
Get rates
A water park and an indoor pool are featured at this smoke-free vacation home. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the hot tub and conveniences like a garden and laundry facilities.
Pool
Hot Tub
Randolph Inn and Suites

Randolph Inn and Suites

2.5 out of 5
890 E Washington Winchester IN
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $121 total per night
$121 total
Jan 8 - Jan 9
Total with taxes and fees
This hotel features an indoor pool and a gym. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A business center, a terrace, and laundry facilities are also on offer.
Pool
Breakfast included
Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70

2.5 out of 5
912 Mendleson Dr Richmond IN
Free Cancellation
Reserve now, pay when you stay
$67 nightly
The price is $75 total per night
$75 total
Jan 9 - Jan 10
Total with taxes and fees
This inn features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like self-serve breakfast and free self parking. A business center, free WiFi in public areas, and dry cleaning are also on offer.
Pool
Hot Tub
Motel 6 Richmond, IN

Motel 6 Richmond, IN

2 out of 5
6030 National Road East Richmond IN
Free Cancellation
Reserve now, pay when you stay
$49 nightly
The price is $55 total per night
$55 total
Jan 8 - Jan 9
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A snack bar/deli and laundry facilities are also provided.
Comfort Suites

Comfort Suites

2.5 out of 5
421 Commerce Road Richmond IN
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $106 total per night
$106 total
Feb 1 - Feb 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Comfort Inn & Suites Muncie Near University

Comfort Inn & Suites Muncie Near University

2.5 out of 5
3400 N Marleon Dr Muncie IN
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $94 total per night
$94 total
Jan 20 - Jan 21
Total with taxes and fees
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like self-serve breakfast and free self parking.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Winchester Speedway

4/5(16 reviews)

Catch an event at Winchester Speedway during your trip to Winchester.

Winchester Speedway

Randolph County Courthouse

4/5(1 review)

After visiting Randolph County Courthouse, make a plan to see the other sights and activities in Winchester.

Randolph County Courthouse

Winchester Golf Club

3.5/5(4 reviews)

Enjoy a round of golf in Winchester at Winchester Golf Club.

Winchester Golf Club

Frequently asked questions

How much are vacation packages to Winchester?
$178 is all you'll need for a memorable vacation in Winchester. Bundle your hotel and flights into a vacation package with Travelocity and see how much the savings start to grow. With these kinds of prices, traveling has never been so accessible.
How long should my Winchester vacation be?
If you need some guidance, most visitors spend roughly 3 nights in Winchester. But to discover the true spirit of this place, stay a bit longer. You'll be able to get to more attractions and really experience the local culture.
Where can I get the best vacation package deals for Winchester?
There are exciting Winchester package deals to be scored with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 worldwide properties? Remember this the next time you're ready to tick another place off your bucket list.
Why should I purchase my Winchester vacation bundle via Travelocity?
We've got a destination for every type of globetrotter, exceptional service and 24/7 customer support. And the icing on the cake is we'll match any better price you come across with our Price Match Guarantee.
Can I save on my Winchester car rental if I combine it with my hotel or flight?
With a Winchester vacation package, you can combine your car, hotel and flight bookings and save some serious money. If you're in the mood to discover the best of this exciting area, why not make a beeline for Indianapolis Motor Speedway? This well-known sight is 70 mi from Winchester. With your own rental car, you'll be there in a flash.
Which airport is best for Winchester?
James M. Cox Dayton Intl. Airport (DAY) is where many travelers arrive. You'll find it 45 mi southeast from downtown Winchester. Alternatively, check out the fares to Fort Wayne Intl. Airport (FWA), which is 55 mi away from central Winchester.
What is there to do in Winchester?
Winchester is overflowing with sights to discover, including Winchester Speedway and Winchester Golf Club. These well-known attractions are at the top of most people's travel schedules.
Where should I stay when visiting Winchester?
If you're searching for someplace comfortable to spend your nights, consider the Randolph Inn and Suites. It's the top choice for many visitors.

Photos of local treasures

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